ES2921724T1 - Lípidos biodegradables para la administración de agentes activos - Google Patents

Lípidos biodegradables para la administración de agentes activos Download PDF

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ES2921724T1
ES2921724T1 ES21212055T ES21212055T ES2921724T1 ES 2921724 T1 ES2921724 T1 ES 2921724T1 ES 21212055 T ES21212055 T ES 21212055T ES 21212055 T ES21212055 T ES 21212055T ES 2921724 T1 ES2921724 T1 ES 2921724T1
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biodegradable
hydrophobic
tail
cationic lipid
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Martin Maier
Muthusamy Jayaraman
Akin Akinc
Shigeo Matsuda
Pachamuthu Kadasamy
Kallanthottathil G Rajeev
Muthiah Manoharan
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Alnylam Pharmaceuticals Inc
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Alnylam Pharmaceuticals Inc
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Abstract

La presente invención se refiere a lípidos catiónicos específicos que comprenden un grupo primario y dos colas hidrofóbicas biodegradables, así como a sus usos en el suministro de moléculas de ácido nucleico. (Traducción automática con Google Translate, sin valor legal)

Claims (15)

REIVINDICACIONES
1. Un lípido catiónico que comprende un grupo principal y dos colas hidrófobas biodegradables, en donde (a) el grupo principal incluye un grupo de cabeza y un resto central al que están unidos directamente tanto las colas hidrófobas biodegradables como el grupo de cabeza, en donde el grupo principal tiene un grupo protonable que tiene un pKa de alrededor de 4 a alrededor de 11, (b) el lípido catiónico tiene una semivida in vivo (ty2) de menos de alrededor de 3 horas en el hígado, (c) el lípido catiónico tiene un valor de logP de al menos 10,1, y
(d) cada cola hidrófoba biodegradable tiene la fórmula
-(cadena hidrófoba)-(grupo biodegradable)-(cadena hidrófoba),
en donde en al menos una cola hidrófoba biodegradable,
(i) la cadena hidrófoba terminal de la cola hidrófoba es un grupo alquilo ramificado, donde la ramificación se da en la posición a respecto del grupo biodegradable;
(ii) el grupo biodegradable está separado desde un extremo de la cola hidrófoba por 6 a 12 átomos de carbono;
(iii) la al menos una cola hidrófoba biodegradable tiene la fórmula -R12-M1-R13, donde R12 es un alquileno C4-C14 o alquenileno C4-C14, M1 es el grupo biodegradable, y R13 es un alquilo C10-C20 ramificado; y (iv) el contenido total de átomos de carbono de la cola -R12-M1-R13 es de 21 a 26.
2. El lípido catiónico de la reivindicación 1, en donde el resto central se selecciona del grupo que consiste en un átomo de carbono central, un átomo de nitrógeno central, un grupo carbocíclico central, un grupo arilo central, un grupo heterocíclico central, y un grupo heteroarilo central.
3. El lípido catiónico de la reivindicación 1, en donde el grupo biodegradable es -OC(O)- o -C(O)O-.
4. El lípido catiónico de la reivindicación 1, en donde la longitud de la cadena de -R12-M1-R13 es como máximo de 21 átomos desde el primer átomo de carbono después del grupo principal hasta un extremo de la cola.
5. El lípido catiónico de la reivindicación 1, en donde
cada grupo biodegradable se selecciona independientemente del grupo que consiste en -OC(O)-, -O(O)O-, -SC(O)-, -C(O)S-, -OC(S)-, -C(S)O-, -S-S-, -C(R5)=N-, -N=C(R5)-, -C(R5)=N-O-, -O-N=C(R5)-, -C(O)(NR5)-, -N(R5)C(O)-, -C(S)(NR5)-, -N(R5)C(O)-, -N(R5)C(O)N(R5)-, -OC(O)O-, -OSi(R5)2O-, -C(O)(CR3R4)C(O)O-,
Figure imgf000002_0001
cada aparición de R3 y R4 es, independientemente, H, halógeno, OH, alquilo, alcoxi, -NH2, R10, alquilamino, o dialquilamino;
cada aparición de R5 es, independientemente, H o alquilo;
cada aparición de R10 se selecciona, independientemente, de polietilen glicol (PEG) y polímeros basados en poli(oxazolina), poli(óxido de etileno), poli(alcohol vinílico), poli(glicerol), poli(N-vinilpirrolidona), poli[N-(2-hidroxipropil)metacrilamida] y poli(aminoácido)s, en donde
(i) el PEG o polímero es lineal o ramificado,
(ii) el PEG o polímero está polimerizado por n subunidades,
(iii) n es un grado de polimerización promediado en número entre 10 y 200 unidades, y
(iv) el compuesto de la fórmula tiene como máximo dos grupos R10; y
R11 es un alquilo C2-C8 o alquenilo C2-C8.
6. El lípido catiónico de la reivindicación 1, en donde en ambas colas hidrófobas biodegradables,
(i) la cadena hidrófoba terminal de la cola hidrófoba es un grupo alquilo ramificado, donde la ramificación se da en la posición a respecto del grupo biodegradable;
(ii) el grupo biodegradable está separado desde un extremo de la cola hidrófoba por 6 a 12 átomos de carbono;
(iii) la cola hidrófoba biodegradable tiene la fórmula -R12-M1-R13, donde -R12 es un alquileno C4-C14 o alquenileno C4-C14, M1 es el grupo biodegradable, y R13 es un alquilo C10-C20 ramificado; y (iv) el contenido total de átomos de carbono de la cola -R12-M1-R13 es de 21 a 26.
7. El lípido catiónico de la reivindicación 1, en donde el lípido catiónico tiene
un valor de logP de al menos alrededor de 10,1, preferiblemente un valor de logP de al menos alrededor de 10,2; un valor de t lípido - tcol de al menos alrededor de 1,4, preferiblemente, un valor de tlípido - tcol de al menos alrededor de 1,75; o
un valor de pKa de alrededor de 4 a alrededor de 7, preferiblemente un valor de pKa de alrededor de 6 a alrededor de 6,5.
8. El lípido catiónico de la reivindicación 1, en donde la al menos una cola hidrófoba biodegradable tiene la fórmula
Figure imgf000003_0001
donde R13 es un grupo alquilo ramificado que tiene de 13 a 17 átomos de carbono, y la longitud total de carbonos desde la cola del primer carbono hasta un extremo de la cola es como máximo de 20.
9. El lípido catiónico de la reivindicación 3, en donde el resto central es un átomo de carbono o nitrógeno central.
10. El lípido catiónico de la reivindicación 9, en donde
ambas colas hidrófobas biodegradables tienen la fórmula -R12-M1-R13;
la longitud de la cadena de -R12-M1-R13 es como máximo de 21 átomos desde el primer átomo después del resto central hasta un extremo de la cola; o
el lípido tiene un pKa de alrededor de 5 a alrededor de 7 cuando se incorpora en una partícula lipídica.
11. El lípido catiónico de la reivindicación 9, en donde, en al menos una cola hidrófoba,
el número de átomos de carbono entre el resto central y el grupo biodegradable de la cola hidrófoba oscila de 5 a 10; o
el número total de átomos de carbono entre el resto central y un extremo de la cola hidrófoba oscila de 15 a 20.
12. El lípido catiónico de la reivindicación 9, en donde, en al menos una cola hidrófoba,
el grupo biodegradable está separado desde un extremo de la cola hidrófoba por 8 a 12 átomos de carbono, preferiblemente, el grupo biodegradable está separado desde un extremo de la cola hidrófoba por 8 átomos de carbono.
13. El lípido catiónico de la reivindicación 9, en donde en ambas colas hidrófobas biodegradables,
(i) la cadena hidrófoba terminal de la cola hidrófoba es un grupo alquilo ramificado, donde la ramificación se da en la posición a respecto del grupo biodegradable;
(ii) el grupo biodegradable está separado desde un extremo de la cola hidrófoba por 6 a 12 átomos de carbono;
(iii) la cola hidrófoba biodegradable tiene la fórmula -R12-M1-R13, donde R12 es un alquileno C4-C14 o alquenileno C4-C14, M1 es el grupo biodegradable, y R13 es un alquilo C10-C20 ramificado; y (iv) el contenido total de átomos de carbono de la cola -R12-M1-R13 es de 21 a 26.
14. Un lípido catiónico según cualquiera de las reivindicaciones precedentes, en donde el lípido tiene un pKa de alrededor de 5 a alrededor de 7 cuando se incorpora en una partícula lipídica.
15. Un lípido catiónico según cualquiera de las reivindicaciones precedentes para el uso en un método de administración de una molécula de ácido nucleico, y el método comprende administrar a un sujeto una partícula lipídica que comprende
(i) la molécula de ácido nucleico,
(ii) el lípido catiónico; y
(iii) un PEG-lípido.
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